By Dehalogenation Or Dehydrohalogenation Of Adjacent Carbon Atoms In A Compound Patents (Class 570/155)
  • Publication number: 20150011805
    Abstract: The present invention provides a process for purifying a (E)-1-chloro-3,3,3-trifluoropropene composition (OF-1233E composition) in which at hydrogen fluoride and 2-chloro-1,1,1,3,3-pentafluoropropane are contained by bringing the (E)-1-chloro-3,3,3-trifluoropropene composition into contact with a weak base and a method for producing (E)-1-chloro-3,3,3-trifluoropropene composition by distilling the (E)-1-chloro-3,3,3-trifluoropropene composition obtained by such a purification process. This makes it possible to efficiently produce OF-1233E by removing the hydrogen fluoride from the OF-1233E composition, without generating any new component difficult to separate by distillation, and subjecting the resulting composition to distillation.
    Type: Application
    Filed: October 3, 2012
    Publication date: January 8, 2015
    Inventors: Masamune Okamoto, Hideaki Imura, Naoto Takada, Tatsuya Hayasaka
  • Patent number: 8921621
    Abstract: A process for the manufacture of 1-chloro-3,3,3-trifluoropropene (HCFC-1233zd) at commercial scale from the reaction of HCC-240 and HF is disclosed. In one embodiment, HCC-240fa and HF are fed to a reactor operating at high pressure. Several different reactor designs useful in this process include; a stirred-tank reactor (batch and/or continuous flow); a plug flow reactor; a static mixer used as a reactor; at least one of the above reactors operating at high pressure; optionally combined with a distillation column running at a lower pressure; and combinations of the above; and/or with a distillation column. The resulting product stream consisting of 1233zd, HCl, HF, and other byproducts is partially condensed to recover HF by phase separation. The recovered HF phase is recycled to the reactor. The HCl is scrubbed from the vapor stream and recovered as an aqueous solution.
    Type: Grant
    Filed: February 4, 2013
    Date of Patent: December 30, 2014
    Assignee: Honeywell International Inc.
    Inventors: Stephen A. Cottrell, Hsueh Sung Tung, Konstantin A. Pokrovski, Haiyou Wang, Daniel C. Merkel
  • Patent number: 8921622
    Abstract: A process for the selective dehydrofluorination of hydrochlorofluoroalkanes and novel hydrochlorofluoroalkenes is described wherein an effective amount of a catalytically active metal compound is applied which is selected from the group consisting of AlF3??, MgAlxF2+3x?? and MgZryF2+4y??, wherein x and y have, independently of one another, values in the range of from 0 to 0.33 and ? has a value in the range of from 0 to 0.1. Certain hydrofluorochloroalkenes are also described, as well as their use as intermediates in chemical reactions.
    Type: Grant
    Filed: March 31, 2011
    Date of Patent: December 30, 2014
    Assignee: Solvay SA
    Inventors: Johannes Eicher, Ercan Uenveren, Erhard Kemnitz
  • Publication number: 20140378717
    Abstract: The invention relates to a method for preparing olefin fluorine compounds. Specifically, the invention relates to a method for producing a (hydro)fluoroolefin compound, including: (i) in an agitated reactor provided with at least one reactant inlet and at least one outlet, contacting, with potassium hydroxide in an aqueous reaction medium, at least one compound containing three to six carbon atoms, at least two fluorine atoms, and at least one hydrogen atom, with the proviso that at least one hydrogen atom and one fluorine atom are located on adjacent carbon atoms, so as produce the (hydro)fluoroolefin compound, separated in a gaseous state from the reaction medium and from potassium fluoride; (ii) in an aqueous medium, contacting the potassium fluoride formed in step (i) with calcium hydroxide in a second reactor so as to produce potassium.
    Type: Application
    Filed: July 7, 2014
    Publication date: December 25, 2014
    Inventors: Jean-Michel Bossoutrot, Pierre-Marie Sedat
  • Patent number: 8912369
    Abstract: A production method of 1-chloro-3,3,3-trifluoropropene according to the present invention includes bringing a composition containing a compound of the general formula (1): CF3—CH2—CHClX (where X is a fluorine atom or a chlorine atom) into contact with a solid catalyst in the presence of hydrogen chloride. In this production method, the composition containing ozone depleting HCFC such as 3-chloro-1,1,1,3-tetraluoforpropane or 3,3-dichloro-1,1,1-trifluoropropane can be efficiently converted to the 1-chloro-3,3,3-trifluoropropene, which has less influence on the global environment and is useful as a solvent, a cleaning agent, a coolant, a working fluid, a propellant, a raw material for fluorinated resins etc.
    Type: Grant
    Filed: June 27, 2013
    Date of Patent: December 16, 2014
    Assignee: Central Glass Company, Limited
    Inventors: Hideaki Imura, Naoto Takada
  • Publication number: 20140364657
    Abstract: Disclosed is a process for passivating a surface of a dehydrochlorination reactor comprising: stopping a flow of hydrochlorofluoropropane to a reactor, passing a gas mixture comprising hydrogen gas through the reactor at a temperature of at least 25° C. for a period of time sufficient to restore the selectivity of a dehydrochlorination reaction, stopping the flow of the hydrogen gas mixture, and resuming the flow of hydrochlorofluoropropane to the dehydrochlorination reaction.
    Type: Application
    Filed: January 8, 2013
    Publication date: December 11, 2014
    Applicant: E.I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Xuehui Sun, Mario Joseph Nappa, Haiyou Wang, Haluk Kopkalli
  • Patent number: 8901360
    Abstract: Disclosed is a process for preparing cis-1,1,1,4,4,4-hexafluorobutene comprising the steps of (a) reacting CCl4 with a compound having the formula CF3CX?CXH, where each X is independently halogen or hydrogen, to form a compound having the formula CF3CXClCXHCCl3; (b) fluorinating the compound formed in step (a) to form a compound having the formula CF3CXHCXHCF3; (c) converting the compound formed in step (b) by a reaction selected from the group consisting of dehydrohalogenation, dehalogenation and both reactions, to form a compound having the formula CF3C?CCF3; and (d) catalytically reducing the compound formed in step (c) with hydrogen to form the compound having the formula:
    Type: Grant
    Filed: May 19, 2011
    Date of Patent: December 2, 2014
    Assignee: Honeywell International Inc.
    Inventors: Andrew Joseph Poss, David Nalewajek, Haridasan K. Nair, Michael Van Der Puy
  • Publication number: 20140350309
    Abstract: The present invention relates, in part, to the discovery that the presence of impurities in a reactor for dehydrochlorinating HCFC-244bb to HFO-1234yf results in a reduced conversion rate and/or a selectivity changeover from HFO-1234yf to HCFO-1233xf. By substantially removing such impurities, it is shown that the conversion rate may be improved and selectivity to HFO-C 1234yf via dehydrochlorination of HCFC-244bb is also improved.
    Type: Application
    Filed: October 10, 2012
    Publication date: November 27, 2014
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou Wang, Hsueh Sung Tung, Daniel C. Merkel
  • Publication number: 20140343330
    Abstract: The present invention is related to making hydrofluorocarbons (HCFCs), more specifically, 3,3,3-trifluoropropyne (TFP), from trans-1-chloro-3,3,3-trifluoropropene (trans-1233zd) by contacting the trans-1233zd with a base. Preferably, the base is potassium hydroxide or potassium tert-butoxide, which may or may not be dissolved in as solvent.
    Type: Application
    Filed: May 5, 2014
    Publication date: November 20, 2014
    Inventors: Yian Zhai, Andrew J. Poss, Rajiv R. Singh
  • Patent number: 8889924
    Abstract: The present invention provides a simple three step process for the production of 1,3,3,3-tetrafluoropropene (HFO-1234ze). In the first step, carbon tetrachloride is added to vinyl fluoride to afford the compound CCl3CH2CHClF (HCFC-241fb). HCFC-241fb is then fluorinated with anhydrous HF to afford CF3CH2CHClF (HCFC-244fa) in the second step. Dehydrochlorination of HCFC-244fa, in the third step, affords the desired product, CF3CH?CHF (HFO-1234ze). Following similar chemistry, vinyl chloride may be used in place of vinyl fluoride.
    Type: Grant
    Filed: February 4, 2013
    Date of Patent: November 18, 2014
    Assignee: Honeywell International Inc.
    Inventors: Haridasan K. Nair, Rajiv Ratna Singh, Andrew Joseph Poss, David Nalewajek
  • Patent number: 8884082
    Abstract: A dehydrochlorination process is disclosed. The process involves contacting RfCHClCH2Cl with a carbon catalyst in a reaction zone to produce a product mixture comprising RfCCl?CH2, wherein Rf is a perfluorinated alkyl group.
    Type: Grant
    Filed: February 16, 2012
    Date of Patent: November 11, 2014
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Xuehui Sun, Mario Joseph Nappa
  • Patent number: 8884083
    Abstract: A dehydrochlorination process is disclosed. The process involves contacting RfCHClCH2Cl with a catalyst in a reaction zone to produce a product mixture comprising RfCCl?CH2, wherein said catalyst comprises MY supported on carbon, and wherein Rf is a perfluorinated alkyl group, M=K, Na or Cs, and Y=F, Cl or Br.
    Type: Grant
    Filed: February 10, 2012
    Date of Patent: November 11, 2014
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Xuehui Sun, Mario Joseph Nappa
  • Publication number: 20140316170
    Abstract: The present invention relates, in part, to the discovery that the presence of impurities in 1,1,2,3-tetrachloropropene (1230xa) results in catalyst instability during the fluorination of 1230xa to 2-chloro-3,3,3-trifluoropropene. By substantially removing the impurities, it is shown that the catalyst life is extended and results in improved operation efficiency of the fluorination reaction. Such steps similarly result in an overall improvement in the production of certain hydrofluoroolefins, particularly 2,3,3,3-tetrafluoropropene (1234yf).
    Type: Application
    Filed: October 11, 2012
    Publication date: October 23, 2014
    Inventors: Selma BEKTESEVIC, Daniel C. MERKEL, Mario Joseph NAPPA, Xuehui SUN, Hsueh Sung TUNG, Haiyou WANG
  • Publication number: 20140316169
    Abstract: The present invention discloses a manufacturing process to produce high purity 1234yf from 245eb, which preferably includes the removal of impurities present in 245eb raw material, the dehydrofluorination of 245eb, and the removal of impurities present in final crude product. The disclosed manufacturing process allows the production of a 1234yf product with lower the levels of 1225ye and/or trifluoropropene, preferably in amounts of less than about 500, and 50 ppm, respectively.
    Type: Application
    Filed: June 30, 2014
    Publication date: October 23, 2014
    Inventors: HAIYOU WANG, HSUEH SUNG TUNG, RAJIV R. SINGH, IAN SHANKLAND
  • Patent number: 8865952
    Abstract: The present invention provides a process for producing fluorine-containing alkene represented by Formula (2): Rf1C(Rf2)=CH2 wherein Rf1 and Rf2 are the same or different, and are F, H, F(CF2)n- wherein n is an integer of 1 to 5, or H(CF2)m- wherein m is an integer of 1 to 5, with the proviso that Rf1 and Rf2 are not simultaneously H, by heating fluorine-containing alkane represented by Formula (1): Rf1CF(Rf2))CH3 wherein Rf1 and Rf2 are as defined above, in a gas phase to perform a dehydrofluorination reaction, the dehydrofluorination reaction being carried out in the presence of 5 mol or more of anhydrous hydrogen fluoride per mol of the fluorine-containing alkane. The process of the present invention can significantly enhance the selectivity of fluorine-containing alkene without reducing conversion in the production of fluorine-containing alkene from fluorine-containing alkane, such as fluorine-containing propane.
    Type: Grant
    Filed: February 8, 2011
    Date of Patent: October 21, 2014
    Assignee: Daikin Industries, Ltd.
    Inventors: Yuzo Komatsu, Daisuke Karube
  • Publication number: 20140305161
    Abstract: There is provided a method and an apparatus for efficiently obtaining 2,3,3,3-tetrafluoropropene with low contents of both organic impurities and water. The method for continuously purifying crude 2,3,3,3-tetrafluoropropene containing water and one or more organic impurities, the method including using an apparatus having a distillation column with X stages (3?X, the stage closest to a column top is the first stage) and a unit for cooling and condensing a distillate; supplying the crude 2,3,3,3-tetrafluoropropene to an m-th stage (n+1?m?X, 2?n?X?1) of the distillation column, recirculating at least part of the distillate cooled and condensed in the unit for cooling and condensing to an h-th stage (1?h?n?1) of the distillation column; and taking out a liquid phase part of an n-th stage of the distillation column to obtain a purified product of 2,3,3,3-tetrafluoropropene.
    Type: Application
    Filed: June 16, 2014
    Publication date: October 16, 2014
    Applicant: ASAHI GLASS COMPANY, LIMITED
    Inventors: Satoshi Kawaguchi, Hirokazu Takagi, Masaaki Tsuzaki, Masato Fukushima, Hidekazu Okamoto
  • Publication number: 20140309462
    Abstract: The present disclosure provides a fluorination process which involves reacting a hydrohaloalkene of the formula RfC—Cl?CH2 with HF in a reaction zone in the presence of a fluorination catalyst selected from the group consisting of TaF5 and TiF4 to produce a product mixture containing a hydrohaloalkane of the formula RfCFClCH3, wherein Rf is a perfluorinated alkyl group.
    Type: Application
    Filed: November 9, 2012
    Publication date: October 16, 2014
    Inventors: Mario Joseph NAPPA, Andrew JACKSON, Daniel C. MERKEL
  • Patent number: 8845921
    Abstract: The invention provides a method for separating halocarbons. In particular, a method for separating 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) from 2-chloro-3,3,3-trifluoropropene (HCFC-1233xf) by adding a third component and then separating via conventional distillation. More particularly the invention pertains to a method for separating HCFC-244bb from HCFC-1233xf which are useful as intermediates in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf).
    Type: Grant
    Filed: March 29, 2010
    Date of Patent: September 30, 2014
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh S. Tung, Hang T. Pham, Rajiv R. Singh
  • Patent number: 8846990
    Abstract: The present invention relates, in part, to the discovery that the presence of impurities in a reactor for dehydrochlorinating HCFC-244bb to HFO-1234yf results in selectivity changeover from HFO-1234yf to HCFO-1233xf. By substantially removing such impurities, it is shown that the selectivity to HFO-1234yf via dehydrochlorination of HCFC-244bb is improved.
    Type: Grant
    Filed: October 10, 2012
    Date of Patent: September 30, 2014
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Patent number: 8841493
    Abstract: The subject matter of the invention is a process for preparing fluoroolefin compounds. The invention relates more particularly to a process for producing a (hydro)fluoroolefin compound, which comprises (i) bringing at least one compound comprising from three to six carbon atoms, at least two fluorine atoms and at least one hydrogen atom, on the condition that at least one hydrogen atom and one fluorine atom are located on adjacent carbon atoms, into contact with a solid reactant comprising calcium hydroxide.
    Type: Grant
    Filed: May 4, 2010
    Date of Patent: September 23, 2014
    Assignee: Arkema France
    Inventors: Dominique Guillet, Michel Devic
  • Patent number: 8835698
    Abstract: Disclosed are processes for the production of fluorinated olefins, preferably adapted to commercialization of CF3CF?CH2 (1234yf). In certain preferred embodiments the processes comprise first exposing a compound of Formula (IA) C(X)2?CClC(X)3??(IA) where each X is independently F, Cl or H, preferably CCl2?CClCH2Cl, to one or more sets of reaction conditions, but preferably a substantially single set of reaction conditions, effective to produce at least one chlorofluoropropane, preferably in accordance with Formula (IB): CF3CClX?C(X?)3??Formula (IB) where each X? is independently F, Cl or H, and then exposing the compound of Formula (IB) to one or more sets of reaction conditions, but preferably a substantially single set of reaction conditions, effective to produce a compound of Formula (II) CF3CF?CHZ??(II) where Z is H, F, Cl, I or Br.
    Type: Grant
    Filed: May 7, 2013
    Date of Patent: September 16, 2014
    Assignee: Honeywell International Inc.
    Inventors: Robert C. Johnson, Hsueh S. Tung, Daniel C. Merkel
  • Patent number: 8835700
    Abstract: Disclosed is process for the production of (E) 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(E)) by conducting a continuous reaction without the use of a catalyst. Also disclosed is an integrated system including one or more reactors for producing hydrofluoro olefins, particularly 1233zd(E). The manufacturing process includes six major unit operations: (1) a fluorination reaction of HCC-240fa (in continuous or semi-batch mode) using HF with simultaneous removal of by-product HCl and the product 1233zd(E); (2) recycle of unreacted HCC-240fa and HF together with under-fluorinated by-products back to (1); (3) separation and purification of by-product HCl; (4) separation of excess HF back to (1); (5) purification of final product, 1233zd(E); and (6) isomerization of by-product 1233zd(Z) to 1233zd(E) to maximize the process yield.
    Type: Grant
    Filed: March 4, 2014
    Date of Patent: September 16, 2014
    Assignee: Honeywell International Inc.
    Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Hsueh Sung Tung
  • Patent number: 8829254
    Abstract: The present invention describes a process for making CF3CH?CHF (HFO-1234ze). The process involves the addition of carbon tetrachloride (CCl4) to 1,2-dichloroethylene to form CCl3CHClCHCl2. The compound CCl3CHClCHCl2 thus can then either be treated with HF to produce CF3CHClCHClF as the main product, or it can be converted to CCl2?CHCHCl2 (1230za) by dechlorination. CCl2?CHCHCl2 can be treated with HF such that the main product obtained is CF3CHClCHClF. CF3CH?CHCl may be produced as a by-product, but upon treatment with HF, it affords the compound CF3CHClCHClF. The desired compound, CF3CH?CHF (HFO-1234ze), is obtained as a trans/cis mixture by dehydrochlorination of CF3CH2CHClF or by dechlorination of CF3CHClCHClF.
    Type: Grant
    Filed: February 4, 2013
    Date of Patent: September 9, 2014
    Assignee: Honeywell International Inc.
    Inventors: Haridasan K. Nair, Rajiv Ratna Singh, David Nalewajek, Andrew Joseph Poss
  • Publication number: 20140235903
    Abstract: The present invention relates, in part, to the discovery that the presence of impurities in a reactor for dehydrochlorinating HCFC-244bb to HFO-1234yf results in selectivity changeover from HFO-1234yf to HCFO-1233xf. By substantially removing such impurities, it is shown that the selectivity to HFO-1234yf via dehydrochlorination of HCFC-244bb is improved.
    Type: Application
    Filed: October 10, 2012
    Publication date: August 21, 2014
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Patent number: 8809601
    Abstract: The invention relates to a method for preparing olefin fluorine compounds.
    Type: Grant
    Filed: May 19, 2010
    Date of Patent: August 19, 2014
    Assignee: Arkema France
    Inventors: Jean-Michel Bossoutrot, Pierre-Marie Sedat
  • Patent number: 8791309
    Abstract: In accordance with the present invention, processes of synthesizing 3,3,3-trifluoropropyne from 1,3,3,3-tetrafluoropropene, 1-chloro-3,3,3-trifluoropropene, and/or 1,1,1,3,3-pentafluoropropane are provided.
    Type: Grant
    Filed: December 6, 2013
    Date of Patent: July 29, 2014
    Assignee: Honeywell International Inc.
    Inventors: Yian Zhai, Andrew J. Poss, Rajiv R. Singh, David Nalewajek
  • Patent number: 8766020
    Abstract: The present invention discloses a manufacturing process to produce high purity 1234yf from 245eb, which preferably includes the removal of impurities present in 245eb raw material, the dehydrofluorination of 245eb, and the removal of impurities present in final crude product. The disclosed manufacturing process allows the production of a 1234yf product with lower the levels of 1225ye and/or trifluoropropene, preferably in amounts of less than about 500, and 50 ppm, respectively.
    Type: Grant
    Filed: July 28, 2009
    Date of Patent: July 1, 2014
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung, Rajiv R. Singh, Ian Shankland
  • Publication number: 20140179961
    Abstract: In accordance with the present invention, processes of synthesizing 3,3,3-trifluoropropyne from 1,3,3,3-tetrafluoropropene, 1-chloro-3,3,3-trifluoropropene, and/or 1,1,1,3,3-pentafluoropropane are provided.
    Type: Application
    Filed: December 6, 2013
    Publication date: June 26, 2014
    Applicant: Honeywell International Inc.
    Inventors: Yian Zhai, Andrew J. Poss, Rajiv R. Singh, David Nalewajek
  • Patent number: 8716538
    Abstract: Provided is a process for purifying an organic feedstock comprising (a) distilling a raw organic feedstock comprising hydrogen fluoride, 2-chloro-1,1,1,2-tetrafluoropropane, and 2-chloro-3,3,3-trifluoropropene to produce a first distillate stream comprising an azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoropropene, and hydrogen fluoride, and a first bottoms stream rich in hydrogen fluoride; (b) cooling said first distillate stream to produce an intermediate composition comprising an organic layer rich in 2-chloro-1,1,1,2-tetrafluoropropane and 2-chloro-3,3,3-trifluoropropene, and an acid layer rich in hydrogen fluoride; and, optionally but preferably, (c) distilling said organic layer to produce a second distillate stream comprising an azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoropropene, and hydrogen fluoride, and a second bottoms stream comprising a purified organic feedstock substantially free of hydrogen fluoride.
    Type: Grant
    Filed: August 2, 2013
    Date of Patent: May 6, 2014
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh S. Tung
  • Patent number: 8710282
    Abstract: The instant invention relates, at least in part, to a method increasing the cost efficiency for dehydrohalogenation production of a fluorinated olefin by recovering and recycling spent dehydrohalogenation agent. In one aspect, the present invention relates to dehydrohalogenating a fluorinated alkane (e.g. pentafluoropropane and/or hexafluoropropane) in the presence of a dehydrohalogenating agent to produce a fluorinated olefin (e.g. tetrafluoropropenes and/or pentafluoropropenes). Removal of spent dehydrohalogenating agent from the reactor allows for facile separation of organic and dehydrohalogenating agent, the latter of which is recycled.
    Type: Grant
    Filed: September 9, 2011
    Date of Patent: April 29, 2014
    Assignee: Honeywell International Inc.
    Inventors: Selma Bektesevic, Hsueh Sung Tung, Haluk Kopkalli
  • Patent number: 8704017
    Abstract: Disclosed is process for the production of (E) 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(E)) by conducting a continuous reaction without the use of a catalyst. Also disclosed is an integrated system for producing hydrofluoro olefins, particularly 1233zd(E). The manufacturing process includes six major unit operations: (1) a fluorination reaction of HCC-240fa (in continuous or semi-batch mode) using HF with simultaneous removal of by-product HCl and the product 1233zd(E); (2) recycle of unreacted HCC-240fa and HF together with under-fluorinated by-products back to (1); (3) separation and purification of by-product HCl; (4) separation of excess HF back to (1); (5) purification of final product, 1233zd(E); and (6) isomerization of by-product 1233zd(Z) to 1233zd(E) to maximize the process yield.
    Type: Grant
    Filed: August 29, 2011
    Date of Patent: April 22, 2014
    Assignee: Honeywell International Inc.
    Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Hsueh Sung Tung
  • Patent number: 8697922
    Abstract: Described is a method for producing fluoropropenes of formula CF3CX?CX2 wherein each X is F or H, at least one X is H, and at least one X is F, comprising pyrolyzing a hydrofluorochloropropane of formula CF3CXYCX2Y, wherein each X is F or H, at least one X is H, and at least one X is F, and one Y is Cl and the other Y is H, in the gas-phase in a reaction vessel, maintained at a temperature high enough to effect the pyrolysis of said hydrofluorochloropropane to said fluoropropene, wherein the selectivity for the production of the fluoropropene is at least 80%, in the absence of a catalyst.
    Type: Grant
    Filed: May 23, 2012
    Date of Patent: April 15, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventor: Mario Joseph Nappa
  • Patent number: 8680346
    Abstract: The subject of the invention is a process for the preparation of 2,3-dichloro-1,1,1-trifluoropropane by chlorination of 3,3,3-trifluoropropene at a pressure greater than 2 bar. Application in the synthesis of 1234yf.
    Type: Grant
    Filed: September 11, 2009
    Date of Patent: March 25, 2014
    Assignee: Arkema France
    Inventors: Anne Pigamo, Michel Devic, Laurent Wendlinger
  • Publication number: 20140066670
    Abstract: Disclosed is a reactor and agitator useful in a high pressure process for making 1-chloro-3,3,3-trifluoropropene (1233zd) from the reaction of 1,1,1,3,3-pentachloropropane (240fa) and HF, wherein the agitator includes one or more of the following design improvements: (a) double mechanical seals with an inert barrier fluid or a single seal; (b) ceramics on the rotating faces of the seal; (c) ceramics on the static faces of seal; (d) wetted o-rings constructed of spring-energized Teflon and PTFE wedge or dynamic o-ring designs; and (e) wetted metal surfaces of the agitator constructed of a corrosion resistant alloy.
    Type: Application
    Filed: March 14, 2013
    Publication date: March 6, 2014
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventor: Stephen A. Cottrell
  • Patent number: 8664456
    Abstract: Disclosed is an integrated process to co-produce trans-1-chloro-3,3,3-trifluoro-propene (1233zd (E)), trans-1,3,3,3-tetrafluoropropene (1234ze (E)), and 1,1,1,3,3-pentafluoropropane (245fa). Overall the co-production is a three-step process. The chemistry involves the steps of: (1) the reaction of 1,1,1,3-tetrachloropropene and/or 1,1,3,3-tetrachloropropene with anhydrous HF in excess in a liquid-phase catalyzed reactor in such a way as to co-produce primarily 1233zd (E) and 244fa (plus by-product HCl); an optionally (2) the 244fa stream can then be used to directly produce any (or all) of the following desired products; (a) the 244fa stream can be dehydrochlorinated to produce the desired second product 1234ze (E); and/or (b) the 244fa stream can be dehydrofluorinated to produce 1233zd (E) if more of that product is desired; and/or (c) the 244fa stream can be further fluorinated to form 245fa.
    Type: Grant
    Filed: March 28, 2012
    Date of Patent: March 4, 2014
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung
  • Patent number: 8653309
    Abstract: Trans-1233zd, the trans-isomer of 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) can be used as blowing agents, solvents, cleaning agents, as well as monomers of macromolecule compounds, and can be prepared through the dehydrochlorination of 1,1,1-trifluoro-3,3-dichloropropane (HCFC-243fa) with the help of a catalyst. The present invention is directed to an integrated process is proposed to produce trans-1233zd from 243fa, which is consisted of the following four major unit operations: (1) Catalytic dehydrochlorination of 243fa into trans/cis-1233zd, (2) HCl recovery, (3) Catalytic isomerization of cis-1233zd into trans-1233zzd, and (4) Isolation of trans-1233zd.
    Type: Grant
    Filed: April 20, 2011
    Date of Patent: February 18, 2014
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Patent number: 8648222
    Abstract: There is provided methods for making a catalyst composition represented by the formula MX/M?F2 wherein MX is an alkali metal halide; M is an alkali metal ion selected from the group consisting of Li+, Na+, K+, Rb+, and Cs+; X is a halogen ion selected from the group consisting of F?, Cl?, Br?, and I?; M?F2 is a bivalent metal fluoride; and M? is a bivalent metal ion. There is also a method for making a fluorinated olefin.
    Type: Grant
    Filed: July 6, 2011
    Date of Patent: February 11, 2014
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Publication number: 20140024864
    Abstract: A subject of the invention is a compound of formula (I) XCFzR3-z in which: in which X represents a branched or linear unsaturated hydrocarbon radical having up to 5 carbon atoms, unsubstituted or substituted, R represents Cl, F, Br, I or H, Z is equal to 1, 2 or 3, and the bio-carbon content of which is at least 1%. A subject of the invention is also processes for the preparation of this compound.
    Type: Application
    Filed: September 4, 2013
    Publication date: January 23, 2014
    Applicant: Arkema France
    Inventor: Jean-Luc DUBOIS
  • Publication number: 20140018582
    Abstract: The present disclosure relates to processes for reducing the concentration of RfC?CX impurities in fluoroolefins. The process involves: contacting a mixture comprising at least one fluoroolefin and at least one RfC?CX impurity with at least one amine to reduce the concentration of the at least one RfC?CX impurity in the mixture; wherein Rf is a perfluorinated alkyl group, and X is H, F, Cl, Br or I. The present disclosure also relates to processes for making at least one hydrotetrafluoropropene product selected from the group consisting of CF3CF?CH2, CF3CH?CHF, and mixtures thereof and reducing the concentration of CF3C?CH impurity generated during the process. The present disclosure also relates to processes for making at least one hydrochlorotrifluoropropene product selected from the group consisting of CF3CCl?CH2, CF3CH?CHCl, and mixtures thereof and reducing the concentration of CF3C?CH impurity generated during the process.
    Type: Application
    Filed: June 6, 2013
    Publication date: January 16, 2014
    Inventors: Xuehui SUN, Mario Joseph NAPPA
  • Publication number: 20140012047
    Abstract: The invention provides an improved process to manufacture 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) by reacting 2-chloro-3,3,3,-trifluoropropene (HCFO-1233xf) with hydrogen fluoride, in a liquid phase reaction in the presence of hydrogen chloride and a liquid phase fluorination catalyst. The hydrogen chloride is added into the reaction from an external source at a pressure of about 100 psig or more. The HCFC-244bb is an intermediate in the production of 2,3,3,3-tetrafluoropropene-1 (HFO-1234yf).
    Type: Application
    Filed: September 9, 2013
    Publication date: January 9, 2014
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: DANIEL C. MERKEL, STEPHEN A. COTTRELL, ROBERT C. JOHNSON
  • Patent number: 8624067
    Abstract: The present invention provides a process for preparing 2-chloro-3,3,3-trifluoropropene including subjecting, in the absence of a catalyst, at least one chlorine-containing compound selected from the group consisting of chloropropane represented by formula (1): CClX2CHClCH2Cl, wherein each X is the same or different and each represents Cl or F, chloropropene represented by formula (2): CClY2CCl?CH2, wherein each Y is the same or different and each represents Cl or F, and chloropropene represented by formula (3): CZ2?CClCH2Cl, wherein each Z is the same or different and each represents Cl or F, to a reaction with hydrogen fluoride under heating in a gas phase. According to the present invention, 2-chloro-3,3,3-trifluoropropene (HCFC-1233xf) can be effectively prepared by an easy and economically advantageous process that is suitable for industrial scale production.
    Type: Grant
    Filed: April 21, 2010
    Date of Patent: January 7, 2014
    Assignee: Daikin Industries, Ltd.
    Inventors: Masatoshi Nose, Atsushi Suzuki, Tsuneo Yamashita, Kenichi Katsukawa
  • Patent number: 8618340
    Abstract: Disclosed is a process for the manufacture of HFO-1234yf from TCP in three integrated steps that include hydrofluorination of TCP (tetrachloropropene) to HCFC-1233xf in the vapor phase followed by hydrofluorination of HCFC-1233xf to HCFC-244bb in the liquid phase which is then followed by dehydrochlorination in liquid or vapor phase to produce HFO-1234yf. The vapor phase hydrofluorination is carried out at a higher pressure than the liquid phase hydrofluorination, thereby eliminating the need for compression and/or intermediate recovery. Also, any HCl generated from this reaction is fed to the liquid phase hydrofluorination section to promote agitation and mixing. This results in a more economical process from an initial capital and operating cost versus conducting the 3-steps sequentially.
    Type: Grant
    Filed: November 3, 2009
    Date of Patent: December 31, 2013
    Assignee: Honeywell International Inc.
    Inventors: Haluk Kopkalli, Yuon Chiu, Stephen A. Cottrell, Hsueh Sung Tung, Kevin Uhrich
  • Publication number: 20130338408
    Abstract: Provided is a process for purifying an organic feedstock comprising (a) distilling a raw organic feedstock comprising hydrogen fluoride, 2-chloro-1,1,1,2-tetrafluoropropane, and 2-chloro-3,3,3-trifluoropropene to produce a first distillate stream comprising an azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoropropene, and hydrogen fluoride, and a first bottoms stream rich in hydrogen fluoride; (b) cooling said first distillate stream to produce an intermediate composition comprising an organic layer rich in 2-chloro-1,1,1,2-tetrafluoropropane and 2-chloro-3,3,3-trifluoropropene, and an acid layer rich in hydrogen fluoride; and, optionally but preferably, (c) distilling said organic layer to produce a second distillate stream comprising an azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoropropene, and hydrogen fluoride, and a second bottoms stream comprising a purified organic feedstock substantially free of hydrogen fluoride.
    Type: Application
    Filed: August 2, 2013
    Publication date: December 19, 2013
    Applicant: Honeywell International Inc.
    Inventors: DANIEL C. MERKEL, KONSTANTIN A. POKROVSKI, HSUEH S. TUNG
  • Patent number: 8609907
    Abstract: One or more hydrochlorofluoroalkenes can be produced by dehydrofluorination of a hydrochlorofluoroalkane over a X-ray amorphous high surface metal fluoride or a X-ray amorphous or weakly crystalline metal oxide fluoride wherein the metal is selected from the 2nd, 3rd or 4th main group or any subgroup of the periodic system of elements. High-surface aluminum fluoride or aluminum oxide fluoride are especially suitable as catalysts. For example, CF3CH2CHClF is reacted to produce CF3CH?CHCl, and CF3CH2CClFCH3 is reacted to form CF3CH2CCl?CH2 and/or CF3CH?CClCH3.
    Type: Grant
    Filed: November 20, 2009
    Date of Patent: December 17, 2013
    Assignee: Solvay Fluor GmbH
    Inventors: Johannes Eicher, Wolfgang Kalbreyer, Ercan Uenveren
  • Publication number: 20130274528
    Abstract: The invention relates to a process for preparing 2,3,3,3-tetrafluoropropene (CF3CF?CH2), performed using the steps of dehydrohalogenating 1,1,1,2,2-pentafluoropropane (CH3CF2CF3, HFC-245ca) 1,1,1,2-tetrafluoro-2-chloropropane, 1,1,1,2,3-pentafluoropropane (CH2FCHFCF3, HFC-245eb) and/or 1,1,1,2-tetrafluoro-3-chloropropane in the presence of a base, and converting a trifluorodichloropropane or a difluorotrichloropropane or a fluorotetrachloropropane to CH3CF2CF3, 1,1,1,2-tetrafluoro-2-chloropropane, CH2FCHFCF3, and/or 1,1,1,2-tetrafluoro-3-chloropropane.
    Type: Application
    Filed: June 13, 2013
    Publication date: October 17, 2013
    Applicant: MEXICHEM AMANCO HOLDING S.A. DE C.V.
    Inventors: Andrew Paul Sharratt, Robert Elliott Low, John Charles McCarthy
  • Patent number: 8558041
    Abstract: The present invention provides isothermal multitube reactors suitable for the production of chlorinated and/or fluorinated propene and higher alkenes from the reaction of chlorinated and/or fluorinated alkanes and chlorinated and/or fluorinated alkenes. The reactors utilize a feed mixture inlet temperature at least 20° C. different from a desired reaction temperature.
    Type: Grant
    Filed: October 8, 2010
    Date of Patent: October 15, 2013
    Assignee: Dow Global Technologies, LLC
    Inventors: Max M. Tirtowidjojo, Hua Bai, Debashis Chakraborty, Juergen Eiffler, Heinz Groenewald, Kurt F. Hirsekorn, Manfred Kokott, William J. Kruper, Jr., Thomas U. Luebbe, Avani M. Patel, Shirley S. Sexton, Peter Wenzel, Marcus Wobser
  • Publication number: 20130261353
    Abstract: Disclosed is an integrated manufacturing process to co-produce (E) 1-chloro-3,3,3-trifluoropropene, (E) 1,3,3,3-tetrafluoropropene, and 1,1,1,3,3-pentafluoro-propane starting from a single starting feed material or a mixture of unsaturated hydrochloro-carbon feed materials comprising 1,1,1,3-tetrachloropropene and/or 1,1,3,3-tetrachloro-propene. The process includes a combined liquid or vapor phase reaction/purification operation which directly produces (E) 1-chloro-3,3,3-trifluoro-propene (1233zd (E)) from these feed materials, which may also include 240fa. In the second liquid phase fluorination reactor 1233zd (E) is contacted with HF in the presence of catalyst to produce 1,1,1,3,3-pentafluoropropane (245fa) with high conversion and selectivity. A third reactor is used for dehydrofluorination of 245fa to produce (E) 1,3,3,3-tetrafluoro-propene (1234ze (E)) by contacting in the liquid phase with a caustic solution or in the vapor phase using a dehydrofluorination catalyst.
    Type: Application
    Filed: March 28, 2012
    Publication date: October 3, 2013
    Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Haiyou Wang, Hsueh Sung Tung
  • Patent number: 8546623
    Abstract: The invention relates to a process for preparing a C3-6 hydrofluoroalkene comprising dehydrohalogenating a C3-6 hydrohalofluoroalkane in the presence of a zinc/chromia catalyst.
    Type: Grant
    Filed: October 3, 2007
    Date of Patent: October 1, 2013
    Assignee: Mexichem Amanco Holding S.A. de C.V.
    Inventors: Andrew Paul Sharratt, Leslie Seddon
  • Publication number: 20130253235
    Abstract: Disclosed are processes for the production of fluorinated olefins, preferably adapted to commercialization of CF3CF?CH2 (1234yf). In certain preferred embodiments the processes comprise first exposing a compound of Formula (IA) C(X)2?CClC(X)3??(IA) where each X is independently F, Cl or H, preferably CCl2?CClCH2Cl, to one or more sets of reaction conditions, but preferably a substantially single set of reaction conditions, effective to produce at least one chlorofluoropropane, preferably in accordance with Formula (IB): CF3CClX?C(X?)3??Formula (IB) where each X? is independently F, Cl or H, and then exposing the compound of Formula (IB) to one or more sets of reaction conditions, but preferably a substantially single set of reaction conditions, effective to produce a compound of Formula (II) CF3CF?CHZ??(II) where Z is H, F, Cl, I or Br.
    Type: Application
    Filed: May 7, 2013
    Publication date: September 26, 2013
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: ROBERT C. JOHNSON, HSUEH S. TUNG, DANIEL C. MERKEL
  • Publication number: 20130245341
    Abstract: Process of catalytic fluorination in liquid phase of product 2-chloro-3, 3, 3-trifluoropropene into product 2-chloro-1, 1, 1, 2-tetrafluoropropane, with an ionic liquid based catalyst. Process for manufacturing 2, 3, 3, 3-tetrafluoropropene.
    Type: Application
    Filed: October 25, 2010
    Publication date: September 19, 2013
    Inventors: Anne Pigamo, Laurent Wendlinger, Phillppe Bonnet